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Issue 21, 2015
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Selective chemical modification of DNA with alkoxy- and benzyloxyamines

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Abstract

A new method for the selective chemical modification of DNA at cytosine nucleobases using alkoxy- and benzyloxyamines is presented. It is shown that in particular benzyloxyamines are effective DNA modifying agents, giving rise to almost exclusive formation of the mono addition products. By using a bifunctional derivative, that is, p-azidobenzyloxyamine hydrochloride, an azide moiety, which is a convenient handle for further functionalization, could be introduced into the DNA. The azido modified DNA was then further reacted in a copper(I)-monophos catalysed 1,3-dipolar cycloaddition. These results illustrate the potential of the presented method for application in site and chemo-selective modification of DNA.

Graphical abstract: Selective chemical modification of DNA with alkoxy- and benzyloxyamines

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Supplementary files

Article information


Submitted
25 Mar 2015
Accepted
29 Apr 2015
First published
29 Apr 2015

This article is Open Access

Org. Biomol. Chem., 2015,13, 6059-6065
Article type
Paper
Author version available

Selective chemical modification of DNA with alkoxy- and benzyloxyamines

L. Gjonaj and G. Roelfes, Org. Biomol. Chem., 2015, 13, 6059
DOI: 10.1039/C5OB00595G

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